Advice: Going from roommates to romance

July 24, 2013|Anna Pulley, @annapulley | RedEye's sex columnist

I have a new female roommate that moved in a month ago, and I have a crush on her. I have taken her to a movie once, but I'm shy and never asked personal questions during or after the movie. How should I approach her without making her uncomfortable? I heard from my sister (also my roommate) that she is seeing someone. I'm in my early 30s, and she is in her early 20s. What's my best way to ask her out again for dinner or drinks or some summer events? Note: She is a very outgoing person, goes out a lot and likes to party out with "friends.” I need help with these situations; she is a pretty young lady with a great personality. Please help me Anna!

OK! I’ll help! My advice to you is this: Wait. It’s only been a month, Chandler. You have a crush, but in a few more months you might realize you don’t want to play house with this gal after all. Hell, you don’t even know for sure if she’s dating anyone or not. Such guesswork does not a fulfilling relationship make (except maybe a horizontal one).

You should get to know her a little better before you try to butter her popcorn, if you catch my drift. The good news is that hanging out with and getting to know a roommate is far easier than getting to know a random crush--because they are accessible to you and you see them semi-naked on the regular. Congrats! You have home-court advantage. But for now, quit your dribbling and learn about what makes this “pretty young lady with a great personality” tick. In a platonic manner. You can do so any way you please--whether it’s fixing her dinner at home, splitting a Swiss Milk sundae from Margie’s Candies or just chatting her up as you pass each other on the way to the bathroom. But don’t skip this step!

Once you know her favorite “Sopranos” character, how often she posts pictures of her feet on Instagram, and at least one embarrassing story involving rum and a Flowbee, then and only then should you consider taking it up a notch. And while you’re getting to know her, pay attention. Does she seem genuinely interested in what you say? Does she flirt with you? Does she talk about other dudes she has crushes on? Read the cues. If she’s sending you big flashing “do not pass go” signals, then you’ll know it’s time to move on.

Waiting also has the added bonus of getting her lease a little closer to expiring, should you make a pass at her and things get awkward. As I’ve said before: Breaking up may be hard to do, but packing up is harder. Think carefully about whether cohabi-dating is going to make your life really hard (as opposed to making less important things really hard).